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Structure and Chemistry of Sulfur Tetrafluoride James

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Structure and Chemistry of Sulfur Tetrafluoride James STRUCTURE AND CHEMISTRY OF SULFUR TETRAFLUORIDE JAMES T. GOETTEL B.Sc., University of Alberta, 2011 A Thesis Submitted to the School of Graduate Studies of the University of Lethbridge in Partial Fulfilment of the Requirements for the Degree MASTER OF SCIENCE Department of Chemistry and Biochemistry University of Lethbridge LETHBRIDGE, ALBERTA, CANADA © James T. Goettel, 2013 ABSTRACT Sulfur tetrafluoride was shown to be a useful reagent in preparing salts of VII − V − VII − Re O2F4 , I OF4 , and I O2F4 . Sulfur tetrafluoride reacts with oxo-anions in acetonitrile or anhydrous HF (aHF) via fluoride-oxide exchange reactions to quantitatively form oxide fluoride salts, as observed by Raman and 19F NMR spectroscopy. Pure Ag[ReO2F4] as well as the new CH3CN coordination compounds [Ag(CH3CN)2][ReO2F4] and [Ag(CH3CN)4][ReO2F4]•CH3CN were prepared. The latter was characterized by single-crystal X-ray diffraction. The reaction of [N(CH3)4]IO3 with SF4 in acetonitrile gave the new [N(CH3)4][IOF4] salt. Sulfur tetrafluoride forms Lewis acid-base adducts with pyridine and its derivatives, i.e., 2,6-dimethylpyridine, 4-methylpyridine and 4- dimethylaminopyridine, which have recently been identified in our lab. In the presence of HF, the nitrogen base in the SF4 base reaction systems is protonated, which can formally be viewed as solvolysis of the SF4•base adducts by HF. The resulting salts have been studied by Raman spectroscopy and X-ray crystallography. + − Crystal structures were obtained for pyridinium salts: [HNC5H5 ]F •SF4, + − − + − [HNC5H5 ]F [HF2 ]•2SF4; 4-methylpyridinium salt: [HNC5H4(CH3) ]F •SF4, + − [HNC5H4(CH3) ][HF2 ]; 2,6-dimethylpyridinium salt: + − − [HNC5H3(CH3)2 ]2[SF5 ]F •SF4; 4-dimethylaminopyridinium salts: + − − + − [HNC5H4N(CH3)2 ]2[SF5 ]F •CH2Cl2, [NC5H4N(CH3)2 ][HF2 ]•2SF4; and the 4,4’- + − 2+ − bipyridinium salts: [HNH4C5−C5H4N ]F •2SF4, [HNH4C5−C5H4NH ]2F •4SF4. These structures exhibit a surprising range of bonding modalities between SF4 and fluoride and provide an extensive view of SF4 in the solid state. iii For the first time, the solid-state structure of SF4 was elucidated by single- crystal X-ray diffraction. The structure can best be described as a network with weak intermolecular S---F contacts formed exclusively by the axial fluorines that exhibit more ionic character. A similar structural motif was found in the novel + − − [HNC5H3(CH3)2 ]2[SF5 ]F •4SF4 salt which contains layers of SF4. Adduct formation of SF4 with oxygen-bases was observed for the first time. These SF4•O-base adducts (SF4•OC4H8, SF4•(OC4H8)2, SF4•(CH3OCH2)2, SF4•(O=C5H8)2) were synthesized, isolated, and characterized at low temperatures. The structures were elucidated by X-ray crystallography and Raman spectroscopy. The characterization of the SF4•ketone adduct (SF4•O=C5H4) is of great significance, since SF4 can serve as a fluorinating agent towards carbonyl groups. These adducts offer the first extensive view of dative O---S(IV) bonds. iv ACKNOWLEDGEMENTS I would like to thank my supervisor, Prof. Michael Gerken, for his superior mentorship during the past few years. Michael always provided me with the highest quality equipment and reagents, and gave me the freedom to explore a wide range of chemistry. His expertise, enthusiasm, dedication, and overall professionalism made him the ultimate supervisor for me. I would like to thank the other members of my committee, Prof. Paul Hayes and Prof. Paul Hazendonk, for taking the time out of their busy schedules, especially considering the time commitment associated with newborns! I would like to thank my external examiner, Prof. Jennifer Love, for traveling a great distance for my defence, and for her time spent reviewing my Thesis. I am grateful to Kris and Heinz Fischer for all their hard work in maintaining our instruments and especially for fixing the X-ray diffractometer. I am grateful to Tony Montina for fixing the NMR spectrometer. I would like to thank all the members of the Gerken group, Praveen, Tyler, Rudy, Nathan, and Doug, for support and friendship in and outside of the lab. Special thanks to Nathan, who helped with the research presented in Chapter 4 and was a pleasure to supervise. Thank you to the members of the Hayes group, for unofficially adopting me as one of their own. Special thanks to Breanne Kamenz, who made this adoption possible and for keeping me well informed and to Kevin Johnson for his helpful advice. I would like to thank my friends for the fun and enjoyment that contributed to my great work-life balance. v I wish to thank my girlfriend, Boram Kim, for emotional support, care and companionship. Finally I would like the thank my family and my parents, Mark Goettel and Karen Toohey, who have provided financial support, insightful advice, and a loving and caring environment. vi TABLE OF CONTENTS 1 Introduction ........................................................................................................ 1 1.1 Sulfur Fluorides ............................................................................................. 1 1.2 Sulfur Tetrafluoride Chemistry ...................................................................... 7 1.2.1 Lewis-Acid and Fluoride-Ion Donor Properties .................................... 7 1.2.2 Sulfur Tetrafluoride as Reagent in Organic Chemistry. ........................ 9 1.3 Sulfur Fluoride Substituents in Organic and Inorganic Chemistry .............. 13 1.3.1 Pentafluorosulfonyl Substituent, SF5 ................................................... 13 1.3.2 SFx (x = 2-4) ......................................................................................... 15 1.3.3 Sulfur Fluorides as Ligands in Transition Metal Chemistry ................ 16 1.4 Goals of Present Research ........................................................................... 17 2 Experimental .................................................................................................... 28 2.1 General Methods .......................................................................................... 28 2.2 Purification and Preparation of Starting Materials ...................................... 31 2.2.1 Purification of Anhydrous HF, SF4, Acetonitrile................................. 31 2.2.2 Oxo-Anions Salts ................................................................................. 32 2.2.3 Nitrogen Bases ..................................................................................... 32 2.2.4 Purification of Toluene, Diethyl Ether, Pentane, THF ........................ 33 2.2.5 Purification of CH2Cl2, CFCl3, CF2Cl2 ................................................ 33 2.3 Preparation of Oxide Fluoride Salts ............................................................. 33 2.3.1 Preparation of [Ag(CH3CN)x][ReO2F4] where ( x = 0, 2, 4) ............... 33 2.3.2 Preparation of KReO2F4 ....................................................................... 34 2.3.3 Preparation of K[IO2F4] ....................................................................... 34 2.3.4 Preparation of [N(CH3)4][IOF4] ........................................................... 35 2.4 Preparation of Hydrolysis Products of SF4•Nitrogen Base Adducts by HF 36 + − 2.4.1 Preparation of [HNC5H5 ]F •SF4 ......................................................... 36 + − 2.4.2 Preparation of [HNC5H5 ][HF2 ]•2SF4 ................................................ 36 + − 2.4.3 Preparation of [HNC5H4(CH3) ]F •SF4 ............................................... 37 + − − 2.4.4 Preparation of [HNC5H3(CH3)2 ]2[SF5 ]F •SF4 .................................. 37 + − 2.4.5 Preparation of [HNC5H4N(CH3)2 ][HF2 ]•2SF4 .................................. 38 + − − 2.4.6 Preparation of [HNC5H4N(CH3)2 ]2[SF5 ]F •CH2Cl2 ......................... 38 + − 2.4.7 Preparation of [HNH4C5−C5H4N ]F •2SF4 ......................................... 39 vii 2+ − 2.4.8 Preparation of [HNH4C5−C5H4NH ]2F •4SF4 ................................... 39 + − 2.4.9 Crystal Structure of [HNC5H4(CH3) ]HF2 ......................................... 40 2.5 Solid-State Structure of SF4 ......................................................................... 40 + − − 2.5.1 Synthesis of [HNC5H3(CH3)2 ]2F [SF5 ]•4SF4 .................................... 40 2.5.2 X−Ray Crystallography of Neat SF4 ................................................... 41 2.5.3 X−Ray Crystallography of SF4 from CF2Cl2 ....................................... 41 2.6 SF4 Oxygen Base Adducts ........................................................................... 41 2.6.1 Preparation of the SF4•OC4H6 Adduct ................................................. 41 2.6.2 Preparation of the SF4•(OC4H6)2 Adduct ............................................. 42 2.6.3 Preparation of the SF4•(CH3OCH2)2 Adduct ....................................... 42 2.6.4 Preparation of the SF4•(O=C5H8)2 ....................................................... 43 2.6.5 Attempted Preparation of SF4•OEt2 ..................................................... 43 2.6.6 Attempted Preparation of SF4•acetylacetone ....................................... 43 2.6.7 Attempted Preparation of SF4•4-methylcyclohexanone ...................... 43 2.7 Single Crystal X-ray Diffraction .................................................................. 44 2.7.1 Low-Temperature Crystal Mounting ................................................... 44 2.7.1.1 Special Cases .................................................................................. 45 2.7.2 Data Collection ...................................................................................
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